CA1058212A - Process for the preparation of perpropionic acid solutions - Google Patents
Process for the preparation of perpropionic acid solutionsInfo
- Publication number
- CA1058212A CA1058212A CA251,292A CA251292A CA1058212A CA 1058212 A CA1058212 A CA 1058212A CA 251292 A CA251292 A CA 251292A CA 1058212 A CA1058212 A CA 1058212A
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen peroxide
- acid
- reaction
- propionic acid
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/24—Peroxy compounds the —O—O— group being bound between a >C=O group and hydrogen, i.e. peroxy acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Process for the preparation of perpropionic acid solutions ABSTRACT OF THE DISCLOSURE
In the production of perpropionic acid by reaction of hydrogen peroxide and propionic acid in an aqueous medium and in the presence of an acid catalyst, e.g.
sulfuric acid, to produce the peracid and water, the danger of explosion is reduced by employing a molar ratio of hydrogen peroxide to propionic acid of more than 3.5:1, a temperature of up to 50°C, and an initial hydrogen peroxide:water ratio of up to 0.8, and a catalyst concen-tration of 10-40% by weight.
In the production of perpropionic acid by reaction of hydrogen peroxide and propionic acid in an aqueous medium and in the presence of an acid catalyst, e.g.
sulfuric acid, to produce the peracid and water, the danger of explosion is reduced by employing a molar ratio of hydrogen peroxide to propionic acid of more than 3.5:1, a temperature of up to 50°C, and an initial hydrogen peroxide:water ratio of up to 0.8, and a catalyst concen-tration of 10-40% by weight.
Description
f~
The present inven~ion relates to a process for the preparation of perpropionic acid from hydrogen peroxide and propionic acid.
The synthesis of perpropionic acid from hydrogen peroxide and propionic acid is known ~Swern, Organic Peroxides I. Wiley, 1970, page 369-372). The reaction of hydrogen peroxide with propionic acid takes place in the presence of an acid catalyst according to equation ~1) 0 H Q ~ CH CH -COOH -~- ~ H 0~CH CH COOH tl) to give an equilibrium mixture which contains perpropionic acid, propion-ic acid, hydrogen peroxide, water and the acid catalyst. The concen-10 tration of perpropionic acid depends on the concentrations of ~he feed materials and on the molar ratio of hydrogen peroxide and propionic acid in the feed. In general, hydrogen peroxide is used in concentrations of from 30 to 90% by weight, preferably 50 to 70% by weight. Propionic acid is preferably employed in the pure form or as an aqueous solution.
Suitable acid catalysts are the mineral acids, for example sul-phuric acid, acid salts, such as, for example, sodium bisulphate, or cation exchangers based on sulphonated, partially crosslinked polystyrenes in the H ion form. The amount of these catalysts can vary within wide 20 limits.
The mixtures formed according to equation (1) can be used in a known manner for oxidation reactions.
The equilibrium mixtures formed according to equation ~1) also arise as intermediates in processes for the preparation of anhydrous per-propionic acid solutions CDT-OS ~German Published Specification)
The present inven~ion relates to a process for the preparation of perpropionic acid from hydrogen peroxide and propionic acid.
The synthesis of perpropionic acid from hydrogen peroxide and propionic acid is known ~Swern, Organic Peroxides I. Wiley, 1970, page 369-372). The reaction of hydrogen peroxide with propionic acid takes place in the presence of an acid catalyst according to equation ~1) 0 H Q ~ CH CH -COOH -~- ~ H 0~CH CH COOH tl) to give an equilibrium mixture which contains perpropionic acid, propion-ic acid, hydrogen peroxide, water and the acid catalyst. The concen-10 tration of perpropionic acid depends on the concentrations of ~he feed materials and on the molar ratio of hydrogen peroxide and propionic acid in the feed. In general, hydrogen peroxide is used in concentrations of from 30 to 90% by weight, preferably 50 to 70% by weight. Propionic acid is preferably employed in the pure form or as an aqueous solution.
Suitable acid catalysts are the mineral acids, for example sul-phuric acid, acid salts, such as, for example, sodium bisulphate, or cation exchangers based on sulphonated, partially crosslinked polystyrenes in the H ion form. The amount of these catalysts can vary within wide 20 limits.
The mixtures formed according to equation (1) can be used in a known manner for oxidation reactions.
The equilibrium mixtures formed according to equation ~1) also arise as intermediates in processes for the preparation of anhydrous per-propionic acid solutions CDT-OS ~German Published Specification)
2,262,970).
It is therefore extremely important to be able to prepare and handle the said reaction mixtures under explosion-proof conditions.
It is known that aqueous hydrogen peroxide, especially in a con-centrated form, can form, with organic substances, mixtures which are capable of explosion and which present an explosion hazard. The explosi-bility of the lower percarboxylic acids in bulk and in their solutions is -1- ~
also known. Surprisingly~ howeverJ it ~as shown that reaction mixtures such aS are formed by~ the reactlon of hydrogen peroxide wlth propionic acid ln the presence of sulphuric acid according to equation ~1), present an explosion hazard even when 50% strength by weight hydrogen peroxide, that is to say a ratio by weight of hydrogen peroxide: water = 1, and anhydrous propionic acid are used.
Accordingly, the present invention provides a process for the preparation of perpropinoic acid by reaction of hydrogen peroxide with propionlc acid in the presence of sulphuric acid under explosion-proof conditions, c~laracterised in that the reaction of hydrogen peroxide with propionic acid in the presence of sulphuric acid is carried out using a molar ratio of hydrogen peroxide: propionic acid employed of more than 3.5:1, the reaction temperature is restricted to a maximum of 60C and the ratio of hydrogen peroxide ~100% by weight): water by weight before the start of the reaction with propinoic acid is resctricted to a maximum of 0.8, the sulphuric acid concentration in the reacticn mixture being 10-40% by weight.
Contrary to all expectations it has been found, when the reaction mixtures, under conditions of partial, well-defined enclosure in steel bombs, are exposed to heat and when the reaction mixtures are subjected to the detonation shock of a primer charge whilst enclosed in a steel tube (Explosive-stoffe 9, 4 (1961)), that reaction mixtures such as are formed according to equation ~1), are explosive-proof when the molar ratio of hydrogen peroxide: propionic acid employed is restrict~d to more than
It is therefore extremely important to be able to prepare and handle the said reaction mixtures under explosion-proof conditions.
It is known that aqueous hydrogen peroxide, especially in a con-centrated form, can form, with organic substances, mixtures which are capable of explosion and which present an explosion hazard. The explosi-bility of the lower percarboxylic acids in bulk and in their solutions is -1- ~
also known. Surprisingly~ howeverJ it ~as shown that reaction mixtures such aS are formed by~ the reactlon of hydrogen peroxide wlth propionic acid ln the presence of sulphuric acid according to equation ~1), present an explosion hazard even when 50% strength by weight hydrogen peroxide, that is to say a ratio by weight of hydrogen peroxide: water = 1, and anhydrous propionic acid are used.
Accordingly, the present invention provides a process for the preparation of perpropinoic acid by reaction of hydrogen peroxide with propionlc acid in the presence of sulphuric acid under explosion-proof conditions, c~laracterised in that the reaction of hydrogen peroxide with propionic acid in the presence of sulphuric acid is carried out using a molar ratio of hydrogen peroxide: propionic acid employed of more than 3.5:1, the reaction temperature is restricted to a maximum of 60C and the ratio of hydrogen peroxide ~100% by weight): water by weight before the start of the reaction with propinoic acid is resctricted to a maximum of 0.8, the sulphuric acid concentration in the reacticn mixture being 10-40% by weight.
Contrary to all expectations it has been found, when the reaction mixtures, under conditions of partial, well-defined enclosure in steel bombs, are exposed to heat and when the reaction mixtures are subjected to the detonation shock of a primer charge whilst enclosed in a steel tube (Explosive-stoffe 9, 4 (1961)), that reaction mixtures such as are formed according to equation ~1), are explosive-proof when the molar ratio of hydrogen peroxide: propionic acid employed is restrict~d to more than
3.5:1, preerably 3~8-10:1, the reaction temperature is resctricted to a maximum of 60C and the ratio of hydrogen peroxide (100% by weight): water by weight before the start of the reaction with propionic acid is restricted to a maximum of about 0.8, sulphuric acid being used as catalyst.
The reaction temperature in the preparation of the reaction mix-tures is generally between 20 and 60aC, preEerably 30-45C and preferen-tially 35-40.
The present invention i5 illustrated by the tests which follow and the term explosion hazard, which is used there, is also explained.
.~ - 2 -Example:
There are various methods for assessing the explosion haæard of materials. For the present invention, the behaviour when exposed to heat under conditions of partial, well defined enclosure was used to assess the explosion hazard of the reaction mixtures which are formed by the reaction of hydrogen peroxide with propionic acid in the presence of sulphuric acid.
A method for determining the sensitivity of explosive materials towards exposure to heat, which leads to differentiated, comparable numerical values, is to heat the materials in a steel bomb which is closed off by a nozzle plate with a well-defined orifice. The steel bomb is fabricated from deep-drawing sheet metal and has an internal diameter of 24 mm, a length of 75 mm and a wall thickness of 0.5 mm. At its open end, the bomb is provided with a collar. The bomb is closed by a circular nozzle plate provided with a bore. Nozzle plates having the following diameters for the cylindrical outlet orifice for the gases produced by the decomposi-tion are used: l; 1.5; 2; 2.5; 3; 3.5; 4; 5; 6; 8; 10; 12; 14; 16 and 20 mm.
The materials to be investigated are introduced into the steel bombs and, in order to prevent the initiation of a catalytic decomposition, the walls of the steel bomb can be provided with a coating of polyethylene or the like. The volume of the material sample is about 27 ml. The samples are exposed to heat by supplying heat in an amount of, on average, 2.4 kcals/sec. from 4 Teclu burners. With 3 tests, at least one explosion must take place, the bomb being split into 3 or more parts ~"limiting diameter"). The limiting diameter determined in this way is to be regarded as a measure of the heat sensitivity of the material examined. The higher the limiting diameter, the higher is the heat sensitivity. Values of 2-2.5 mm are to be regarded as transition values into the dangerous range, values in excess of 2.5 mm indicating that the reaction mixture is dangerously heat sensitive.
The reaction mixtures investigated were prepared from hydrogen per-oxide of ~he indic~ted concer.tration using anhydrous propionic acid and ~35~2~
concentrated sulphuric acid. The results of the steel bomb tests are given in the table which follows.
As can be seen from the table the range in which there is an explosion hazard is already reached when the ratio by weight of hydrogen peroxide:water in the hydrogen peroxide charged is increased from 0.82 to 1 Ø
=== Ratio by weight Molar ratio Proportion Limiting of hydrogen per of hydrogen of sul- diameter Example oxide:water in peroxide: phuric No. the hydrogen propionic acid % (mm) peroxide charged acid employed ~ __. _ _. __ ___ __ 1 0.82 5 20 2.5 2 0.82 7 20 1.5 3 0.82 10 20 1.0
The reaction temperature in the preparation of the reaction mix-tures is generally between 20 and 60aC, preEerably 30-45C and preferen-tially 35-40.
The present invention i5 illustrated by the tests which follow and the term explosion hazard, which is used there, is also explained.
.~ - 2 -Example:
There are various methods for assessing the explosion haæard of materials. For the present invention, the behaviour when exposed to heat under conditions of partial, well defined enclosure was used to assess the explosion hazard of the reaction mixtures which are formed by the reaction of hydrogen peroxide with propionic acid in the presence of sulphuric acid.
A method for determining the sensitivity of explosive materials towards exposure to heat, which leads to differentiated, comparable numerical values, is to heat the materials in a steel bomb which is closed off by a nozzle plate with a well-defined orifice. The steel bomb is fabricated from deep-drawing sheet metal and has an internal diameter of 24 mm, a length of 75 mm and a wall thickness of 0.5 mm. At its open end, the bomb is provided with a collar. The bomb is closed by a circular nozzle plate provided with a bore. Nozzle plates having the following diameters for the cylindrical outlet orifice for the gases produced by the decomposi-tion are used: l; 1.5; 2; 2.5; 3; 3.5; 4; 5; 6; 8; 10; 12; 14; 16 and 20 mm.
The materials to be investigated are introduced into the steel bombs and, in order to prevent the initiation of a catalytic decomposition, the walls of the steel bomb can be provided with a coating of polyethylene or the like. The volume of the material sample is about 27 ml. The samples are exposed to heat by supplying heat in an amount of, on average, 2.4 kcals/sec. from 4 Teclu burners. With 3 tests, at least one explosion must take place, the bomb being split into 3 or more parts ~"limiting diameter"). The limiting diameter determined in this way is to be regarded as a measure of the heat sensitivity of the material examined. The higher the limiting diameter, the higher is the heat sensitivity. Values of 2-2.5 mm are to be regarded as transition values into the dangerous range, values in excess of 2.5 mm indicating that the reaction mixture is dangerously heat sensitive.
The reaction mixtures investigated were prepared from hydrogen per-oxide of ~he indic~ted concer.tration using anhydrous propionic acid and ~35~2~
concentrated sulphuric acid. The results of the steel bomb tests are given in the table which follows.
As can be seen from the table the range in which there is an explosion hazard is already reached when the ratio by weight of hydrogen peroxide:water in the hydrogen peroxide charged is increased from 0.82 to 1 Ø
=== Ratio by weight Molar ratio Proportion Limiting of hydrogen per of hydrogen of sul- diameter Example oxide:water in peroxide: phuric No. the hydrogen propionic acid % (mm) peroxide charged acid employed ~ __. _ _. __ ___ __ 1 0.82 5 20 2.5 2 0.82 7 20 1.5 3 0.82 10 20 1.0
4 0.82 5 30 2.5 0.82 7 30 2 6 0.82 8 30 2 7 0.82 10 30 1.5 8 0.67 6 20 1.5 9 0.67 10 20 0.67 5 30 2.5 11 0.67 6 30 2 12 0.67 7 30 Z
2Q 13 0.67 10 30 1 14 0.54 4 30 2 0.54 6 30 16 1.0 5.6 20 5 17 1.0 6.7 20 5 18 ~ 1.0 9.4 20 4 19 1.0 4.2 30 5 1.0 6.2 ~ 30 5 21 1 1.0 8.4 1 30 -- 4 - _
2Q 13 0.67 10 30 1 14 0.54 4 30 2 0.54 6 30 16 1.0 5.6 20 5 17 1.0 6.7 20 5 18 ~ 1.0 9.4 20 4 19 1.0 4.2 30 5 1.0 6.2 ~ 30 5 21 1 1.0 8.4 1 30 -- 4 - _
Claims (3)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. Process for the preparation of perpropionic acid by reaction of hydrogen peroxide with propionic acid in the presence of sulphuric acid under explosion-proof conditions, characterised in that the reaction of hydrogen peroxide with propionic acid in the presence of sulphuric acid is carried out using a molar ratio of hydrogen peroxide: propionic acid employed of more than 3.5:1, the reaction temperature is restricted to a maximum of 60°C and the ratio of hydrogen peroxide (100% by weight): water by weight before the start of the reaction with propionic acid is restricted to a maximum of 0.8, the sulphuric acid concentration in the reaction mix-ture being 10-40% by weight.
2. Process according to claim 1, characterised in that the reaction is carried out at a reaction temperature of 30-45°C.
3. Process according to either of claims 1 or 2 characterised in that the molar ratio of hydrogen peroxide: propionic acid is in the range of 3.8:1 to 10:1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2519300A DE2519300C3 (en) | 1975-04-30 | 1975-04-30 | Process for the preparation of perpropionic acid solutions under explosion-proof conditions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1058212A true CA1058212A (en) | 1979-07-10 |
Family
ID=5945453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA251,292A Expired CA1058212A (en) | 1975-04-30 | 1976-04-28 | Process for the preparation of perpropionic acid solutions |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4088679A (en) |
| JP (1) | JPS51133225A (en) |
| AR (1) | AR212705A1 (en) |
| AT (1) | AT344676B (en) |
| BE (1) | BE841210A (en) |
| BG (1) | BG27364A3 (en) |
| BR (1) | BR7602597A (en) |
| CA (1) | CA1058212A (en) |
| CH (1) | CH601223A5 (en) |
| CS (1) | CS189766B2 (en) |
| DD (1) | DD125929A5 (en) |
| DE (1) | DE2519300C3 (en) |
| ES (1) | ES447412A1 (en) |
| FI (1) | FI761182A (en) |
| FR (1) | FR2309532A1 (en) |
| GB (1) | GB1518008A (en) |
| IE (1) | IE42802B1 (en) |
| IL (1) | IL49485A (en) |
| IT (1) | IT1061689B (en) |
| NL (1) | NL7604533A (en) |
| NO (1) | NO142121C (en) |
| PL (1) | PL98406B1 (en) |
| RO (1) | RO74966A (en) |
| SE (1) | SE418081B (en) |
| ZA (1) | ZA7602527D (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2462425A1 (en) * | 1979-08-01 | 1981-02-13 | Air Liquide | METHOD FOR MANUFACTURING STABLE DILUTED SOLUTIONS OF ALIPHATIC CARBOXYLIC PERACIDS |
| JPH05100648A (en) * | 1991-10-04 | 1993-04-23 | Mitsubishi Electric Corp | Test pattern generating device |
| GB2548137A (en) * | 2016-03-09 | 2017-09-13 | Perstorp Ab | Production equipment (I) for production of a caprolactone |
| GB2548138A (en) * | 2016-03-09 | 2017-09-13 | Perstorp Ab | Production equipment (II) for production of a caprolactone |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA744391A (en) * | 1966-10-11 | J. Wenzke Carroll | Method of producing peracids | |
| CA735489A (en) * | 1966-05-31 | Weiberg Otto | Process of producing solutions of pure aliphatic percarboxylic acids | |
| NL267716A (en) * | 1960-08-06 | |||
| FR1352479A (en) * | 1962-04-04 | 1964-02-14 | Fmc Corp | Process for the production of lower aliphatic peracids |
-
1975
- 1975-04-30 DE DE2519300A patent/DE2519300C3/en not_active Expired
-
1976
- 1976-04-28 FI FI761182A patent/FI761182A/fi not_active Application Discontinuation
- 1976-04-28 AT AT311076A patent/AT344676B/en not_active IP Right Cessation
- 1976-04-28 ZA ZA19762527D patent/ZA7602527D/en unknown
- 1976-04-28 RO RO7685936A patent/RO74966A/en unknown
- 1976-04-28 CA CA251,292A patent/CA1058212A/en not_active Expired
- 1976-04-28 IL IL49485A patent/IL49485A/en unknown
- 1976-04-28 SE SE7604888A patent/SE418081B/en not_active IP Right Cessation
- 1976-04-28 BG BG7633052A patent/BG27364A3/en unknown
- 1976-04-28 DD DD192571A patent/DD125929A5/xx unknown
- 1976-04-28 CH CH536176A patent/CH601223A5/xx not_active IP Right Cessation
- 1976-04-28 BE BE2054993A patent/BE841210A/en not_active IP Right Cessation
- 1976-04-28 US US05/678,820 patent/US4088679A/en not_active Expired - Lifetime
- 1976-04-28 BR BR2597/76A patent/BR7602597A/en unknown
- 1976-04-28 NL NL7604533A patent/NL7604533A/en not_active Application Discontinuation
- 1976-04-28 FR FR7612613A patent/FR2309532A1/en active Granted
- 1976-04-28 IE IE894/76A patent/IE42802B1/en unknown
- 1976-04-28 GB GB17183/76A patent/GB1518008A/en not_active Expired
- 1976-04-28 NO NO761474A patent/NO142121C/en unknown
- 1976-04-28 PL PL1976189123A patent/PL98406B1/en unknown
- 1976-04-28 CS CS762789A patent/CS189766B2/en unknown
- 1976-04-28 JP JP51047905A patent/JPS51133225A/en active Granted
- 1976-04-28 IT IT49231/76A patent/IT1061689B/en active
- 1976-04-28 AR AR263147A patent/AR212705A1/en active
- 1976-04-28 ES ES447412A patent/ES447412A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR7602597A (en) | 1976-11-23 |
| JPS5753784B2 (en) | 1982-11-15 |
| JPS51133225A (en) | 1976-11-18 |
| CH601223A5 (en) | 1978-06-30 |
| US4088679A (en) | 1978-05-09 |
| BG27364A3 (en) | 1979-10-12 |
| SE7604888L (en) | 1976-10-31 |
| ATA311076A (en) | 1977-12-15 |
| BE841210A (en) | 1976-10-28 |
| IL49485A (en) | 1978-12-17 |
| IE42802B1 (en) | 1980-10-22 |
| FI761182A (en) | 1976-10-31 |
| NO142121B (en) | 1980-03-24 |
| NO142121C (en) | 1980-07-02 |
| AU1341776A (en) | 1977-11-03 |
| GB1518008A (en) | 1978-07-19 |
| ES447412A1 (en) | 1977-07-01 |
| DD125929A5 (en) | 1977-06-01 |
| IE42802L (en) | 1976-10-30 |
| SE418081B (en) | 1981-05-04 |
| DE2519300C3 (en) | 1979-06-13 |
| FR2309532B1 (en) | 1981-04-30 |
| RO74966A (en) | 1982-09-09 |
| DE2519300B2 (en) | 1978-10-19 |
| PL98406B1 (en) | 1978-05-31 |
| DE2519300A1 (en) | 1976-11-11 |
| NL7604533A (en) | 1976-11-02 |
| AT344676B (en) | 1978-08-10 |
| ZA7602527D (en) | 1977-04-27 |
| IL49485A0 (en) | 1976-06-30 |
| AR212705A1 (en) | 1978-09-15 |
| IT1061689B (en) | 1983-04-30 |
| FR2309532A1 (en) | 1976-11-26 |
| NO761474L (en) | 1976-11-02 |
| CS189766B2 (en) | 1979-04-30 |
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